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Synfacts 2019; 15(03): 0217
DOI: 10.1055/s-0037-1611193
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (–)-Sinulariadiolide

Contributor(s):
Erick M. Carreira
,
Niels Sievertsen
Meng Z, Fürstner A. * Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Total Synthesis of (–)-Sinulariadiolide. A Transannular Approach.

J. Am. Chem. Soc. 2019;
141: 805-809
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Further Information

Publication History

Publication Date:
15 February 2019 (online)

 
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Key words

(–)-sinulariadiolide - Eschenmoser–Tanabe fragmentation - ring-closing alkyne metathesis - trans-hydrostannation - Michael addition

Significance

The tricyclic nor-cembranoid sinulariadiolide was first isolated in 1996 from soft corals found in Okinawa. Fürstner and Meng report the total synthesis of (–)-sinulariadiolide via ring-closing alkyne metathesis followed by an intriguing ­intramolecular reaction cascade.


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Comment

Fragments E and H were accessed from geranic acid (A) and carvone (F). Ring-closing alkyne metathesis and hydrostannation–carbonylation of J gave N. The title compound was accessed by a sequence involving transannular Michael addition.


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